A new anti-inflammatory, analgesic, and antipyretic pharmaceutical composition is disclosed which contains a 3,5-di-tert-butyl-4-hydroxystyrene derivative of the formula: ##STR1## wherein R.sup.1 stands for a group represented by COR.sup.3 [R.sup.3 denotes a group of OR.sup.4 (R.sup.4 is a hydrogen atom or an alkyl group with C.sub.1 .about.C.sub.4), an alkyl group with C.sub.1 .about.C.sub.3, a phenyl group, or an amino group], a nitro group, or an alkylsulfonyl group represented by SO.sub.2 R.sup.5 (R.sup.5 is an alkyl group with C.sub.1 .about.C.sub.3); and R.sup.2 stands for a hydrogen atom, an alkyl group with C.sub.1 .about.C.sub.4, a hydroxyalkyl group with C.sub.1 .about.C.sub.4, a cyano group, or an acyl group represented by COR.sup.6 (R.sup.6 is an alkyl group with C.sub.1 .about.C.sub.3), or its pharmaceutically acceptable salt as an active ingredient in association with pharmaceutical excipients. The pharmaceutical composition has excellent anti-inflammatory, analgesic, and antipyretic activities and low toxicity.
The present invention involves compounds having the structure: ##STR1## wherein: (a) --A.sup.1 is selected from the group consisting of --OH, --H, and --O.sub.2 CR; (b) --A.sup.2 is selected from the group consisting of unsubstituted or substituted, saturated or unsaturated, straight, branched and cyclic alkyl having from 1 to about 10 carbon atoms; (c)--A.sup.3 is selected from --C(CH.sub.3).sub.3, --Si(CH.sub.3).sub.3, and --CF.sub.3 ; and (d) --Y is selected from certain low molecular weight alkyl chains which terminate in specific unsaturated functional groups: ##STR2## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.
The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals. The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier. Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals. Such methods comprise administering to a human or lower animal in need of such treatment a safe and effective amount of an anti-inflammatory agent or composition of the present invention.
The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
The present invention involves compounds having the structure: ##STR1## (a) --A-- is selected from the group consisting of ##STR2## (b) --Y is selected from certain low molecular weight moieties which terminate in specific functional groups: --C.tbd.CH, ##STR3## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.
The subject invention relates to compounds having the structure: ##STR1## wherein (a) X is selected from hydroxy, C.sub.1 to about C.sub.2 alkanoxy, thiol, C.sub.1 to about C.sub.2 alkanylthiol, and halo; (b) R and R' are each independently selected from C.sub.1 to about C.sub.3 straight or branched alkanyl, and C.sub.3 to about C.sub.4 cyclic alkanyl; or R and R' are bonded together to form a C.sub.3 to about C.sub.6 cyclic alkanyl ring, or a C.sub.3 to about C.sub.5 cyclic heteroalkanyl ring having one oxygen or sulfur atom in the ring, the heteroatom not being bonded to the carbon to which X is bonded; and R and R', or the ring formed by them when bonded together, are each, independently, unsubstituted or monosubstituted with a substituent selected from halo, hydroxy, thiol, C.sub.1 to about C.sub.2 alkanoxy, and C.sub.1 to about C.sub.2 alkanylthiol. The subject invention also relates to the pharmaceutical compositions comprising the above compounds, and methods of treating inflammation using the compounds.